


Awkward...

by protectoroffaeries



Category: Hamilton - Miranda
Genre: Awkward Sexual Situations, Awkwardness, F/M, First Time, Horny Teenagers, Kinda, M/M, Multi, NSFW, Poor Pip, Sexual Content, Swearing, Teasing, Teenagers
Language: English
Status: Completed
Published: 2017-03-21
Updated: 2017-03-21
Packaged: 2018-10-08 20:26:15
Rating: Mature
Warnings: Underage
Chapters: 1
Words: 1,517
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10395384
Author URL: https://archiveofourown.org/users/protectoroffaeries/pseuds/protectoroffaeries
Summary: Pip just wants to get laid.





	

**Author's Note:**

> forgive me

The media does a terrible job portraying first times. Beautiful people just magically fall into bed and have great sex. There's no discussion, and yet it's somehow erotic and not awkward in the slightest. Yeah, that isn't how it happens in real life.

Pip has known Theo Burr since kindergarten. She's been his best friend since the beginning of middle school, at least. They've been dating since sophomore year. This - this has been a long time coming, and he still feels awkward as fuck. It's funny because they're casual about it. They'll make sexual jokes and talk about what they think their preferences are.  _ That  _ isn't awkward. It's nice.

Kissing is nice, too. Pip does not shy away from making out like the horny teenager he is, and Theo matches his enthusiasm. He likes touching and groping, and orgasms are  _ mind-blowing;  _ the after-glow and the cuddling is relaxing.

That's cool. Pip's cool with that. He doesn't think he and Theo were too terrible at figuring out those basics.

It's when the clothes start to come off that things go awry.

The problem isn't with Theo; she's fucking beautiful. She has long, wavy hair, which Pip likes best loose (although she always insists on putting it up in public), and deep brown eyes. He wouldn't say they're like, doe’s eyes, because deer always have this vacant look in their eye, but Theo's always sharp. She's smarter than him, hands down, and she's more compassionate, and he's not sure how he got so lucky to have such a wonderful girlfriend who's also his  _ best friend. _

Well… maybe he knows a little. See, Pip is a little vain. He'll admit it. He looks at himself in the mirror a bit too long in the morning; fight him. He thinks he's good-looking. He works out and has the same lean muscle as his papa. He has his papa's freckles, too, which he thinks overall enhance his appearance. And as for his curls, Pip spends a lot of time tending to his hair. He has multiple shampoos. Multiple conditioners. Specialty hair gel. What can he say, curls as a bitch to tame, but once they're under control, they look fantastic.

So Pip doesn't have a problem, really, with taking his shirt off. (And in any case, Theo has seen him shirtless before; they go to the pool constantly over summer break.) Theo takes her shirt off, too, and that isn't weird. It doesn't even get weird when Theo takes her bra off, even though that's uncharted territory.

(Pip is in awe of Theo's boobs. He's sure she would make fun of him if he voiced his initial thoughts, but at first he just thinks they're so… different? He cups them in his hands without having to stretch his fingers. He's not sure what he expected exactly - except that they're not nearly as squishy as he thought they'd be.

They  _ are  _ soft, however, and Pip does comment on that. Because it's unreal, how soft they are. He thought that the “like pillows” thing was some exaggerated, cliché analogy, but he kind of does want to just press his face to them like they're  _ actual fucking pillows. _ Theo giggles and says she puts some sort of lotion on them.)

Okay, so the getting undressed part isn't exactly the problem  _ per say.  _ It's just…

Pip is admiring his amazing girlfriend’s chest, right? He runs his hands over her boobs, rubs her dark nipples and gets some satisfaction when they perk up under his fingertips.

Then Theo's suddenly unbuttoning his pants. He doesn't tell her to stop because he doesn't want to stop; he's actually feeling pretty great down there, half-hard already, and it won't take much to get him all the way there. He lets her push down his pants and his boxer, and then she -  _ holy fuck  _ \- wraps her hand around his dick.

It's amazing what a difference skin-on-skin contact makes. What someone else's warm hand makes. Pip chokes out a half-gasp of approval.

Just when it's getting good, though, it turns sour.

“Pip?” Theo says, and she sounds like she's trying not to laugh, which is every man's nightmare. His dick flags a little, put off by her tone.

“What?”

“You have freckles  _ on  _ your  _ dick,”  _ she says, and then she falls into a fit of laughter. The fucking movies never prepare Pip for this moment, where she's half-naked and  _ laughing _ at his fucking dick, and he's even more naked and fucking annoyed. Now he feels awkward and unsexy and  _ their first time was not supposed to happen like this. _

“Yeah, so?” he huffs. Of course he has freckles on his dick. They're everywhere else. It'd be weird if he  _ didn't  _ have them there.

Theo is still giggling. Pip has no idea what is so fucking funny. “They're just… dick freckles!” she laughs, like that's an explanation.

“So what?”

“I'm sorry,” she blurts, “I don't know why that's so funny. You know how sometimes you just laugh at un-funny things. That's me right now. With your dick freckles.” And then she falls into an uncontrollable fit of giggles again.

“Theo,” he whines, because, really? It's not even that funny. They're just freckles.

“Pip, aw, Philip, don't pout,” she says when she  _ finally _ stops laughing.

“You're laughing at my fucking dick, Theo-” exclaims Pip indignantly, and then he hopes he wasn't too loud because his mother is downstairs. That's just what this moment needs; her barging in to see what's the matter.

“I'm not,” Theo protests, “it's not your dick, Pip, I promise, you have a very nice dick.” As if to prove her point, she sits up and reaches over to take his dick in hand again. “I was laughing because you've such an absurd amount of freckles - hey, I said ‘no pouting’, and I didn't mean it as a bad thing.”

“I've always had an  _ absurd amount _ of freckles!” Theo twists her hand and runs her thumb over the head of his dick, which are probably both ploys to distract him, and they work because his train of thought has completely derailed.

“I know, babe,” Theo says, “which is why it was stupid of me not to think of it before, and then I saw them on your dick and thought  _ of course,  _ and then I couldn't stop laughing. I'm sorry.” She  _ sounds  _ like she's on the verge of laughing again, though.

“Theo,  _ ah,  _ you can't just,  _ fuck,  _ laugh at my dick.”

“Does it have low self-esteem?” she teases, and Pip huffs because yeah, it fucking does. “Want me to kiss it and make it better?”

Oh.  _ Oh.  _ “Yes!”

And just like before, they're so close… and then the bedroom door opens. Pip’ll give the movies that one; sometimes, they show that happening.

What they don't properly convey is how fucking mortifying it is when a parent walks in. Pip's face is  _ on fire, _ and Theo scrambles for something to cover her chest. Papa, comparatively, looks unaffected. “Oh. I didn't know you two were up here.”

“Yeah, that was the point,” Pip snaps, yanking his pants back up and trying to salvage some of his dignity.

“You using protection?” he asks casually like he's not embarrassing the fuck out of them. Or maybe that's his goal exactly. Regardless, Theo answers by motioning to the packets of condoms sitting on Pip's nightstand.

Papa nods, and then he says, “You know where AJ’s mouth guard is? He forgot it this morning.”

Pip is going to  _ murder  _ his little brother. “It's on the desk.”

“Why does AJ need a mouth guard?” Theo asks, apparently not as embarrassed as he is. She's holding Pip's shirt over her chest. Where did hers go?

“Football,” Papa answers. He digs through the clutter piled on the desk until he finds the mouth guard, safe in its little blue case.

“He's playing football?” she says, like she's making fucking small talk. Pip wants to die.

“Yeah, it was a surprise for us, too. Don't let your mother hear you.” Then, thankfully, Papa is gone.

“AJ is a little small and sensitive to play football, don't you think?” says Theo.

“Are you trying to give every man in this family a complex?” Pip asks, even though she's right. AJ  _ is _ tiny for his age, and he cried when James stomped on a caterpillar a few weeks ago.

Theo laughs, and then a silence falls between them. It's not awkward, but it's not comfortable, either. It's silence. Pip is still on his knees with his pants mostly on; Theo's lying back on the bed. Maybe they can get back to what they were doing  _ before  _ Papa walked in…

“You know,” Theo says, “out of the five parents we have between us, it's probably for the best that John was the one to walk in.”

“Yeah.” As embarrassing as it was, Pip would say she's right. Three of their parents would've killed them. Dad would've made it unnecessarily weird.

Theo suddenly bursts out laughing  _ again.  _ She's not usually this giggly - maybe she's nervous?

“What now?” Pip sighs.

_ “He  _ probably has dick freckles, too!”


End file.
